From Heteroaromatic acids and Imines to Azaspirocycles: Stereoselective Synthesis and 3D Shape Analysis

TY - JOUR

T1 - From Heteroaromatic acids and Imines to Azaspirocycles

T2 - Stereoselective Synthesis and 3D Shape Analysis

AU - Chambers, Sarah J

AU - Coulthard, Graeme

AU - Unsworth, William Paul

AU - O'Brien, Peter

AU - Taylor, Richard J K

N1 - © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

PY - 2016

Y1 - 2016

N2 - Heteroaromatic carboxylic acids have been directly coupled with imines using T3P and NEt(i-Pr)2 to form azaspirocycles via intermediate N-acyliminium ions. Spirocyclic indolenines (3H-indoles), azaindolenines, 2H-pyrroles and 3H-pyrroles were all accessed using this metal-free approach. The reactions typically proceed with high diastereoselectivity and 3D shape analysis confirms that the products formed occupy areas of chemical space that are under-represented in existing drugs and high throughput screening libraries.

AB - Heteroaromatic carboxylic acids have been directly coupled with imines using T3P and NEt(i-Pr)2 to form azaspirocycles via intermediate N-acyliminium ions. Spirocyclic indolenines (3H-indoles), azaindolenines, 2H-pyrroles and 3H-pyrroles were all accessed using this metal-free approach. The reactions typically proceed with high diastereoselectivity and 3D shape analysis confirms that the products formed occupy areas of chemical space that are under-represented in existing drugs and high throughput screening libraries.

U2 - 10.1002/chem.201600823

DO - 10.1002/chem.201600823

M3 - Article

C2 - 26918778

SN - 0947-6539

VL - 22

SP - 6496

EP - 6500

JO - Chemistry : A European Journal (Weinheim an der Bergstrasse, Germany)

JF - Chemistry : A European Journal (Weinheim an der Bergstrasse, Germany)

IS - 19

ER -